CA2339622C - Suspension concentrate formulation containing pyrimethanil - Google Patents
Suspension concentrate formulation containing pyrimethanil Download PDFInfo
- Publication number
- CA2339622C CA2339622C CA002339622A CA2339622A CA2339622C CA 2339622 C CA2339622 C CA 2339622C CA 002339622 A CA002339622 A CA 002339622A CA 2339622 A CA2339622 A CA 2339622A CA 2339622 C CA2339622 C CA 2339622C
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- CA
- Canada
- Prior art keywords
- approximately
- formulation according
- component
- polyoxyethylene
- pyrimethanil
- Prior art date
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- Expired - Lifetime
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicinal Preparation (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention provides an aqueous SC formulation comprising: a) 50 to 80 % w/v pyrimethanil; b) 0.2 to 5 % w/v of a polyoxyethylene-polyoxypropylene block copolymer surfactant; and c) 0.2 to 5 %
w/v of a naphthalene formaldehyde condensate surfactant.
We have found that formulations according to the invention surprisingly do not solidify when milled during manufacture and also exhibit a low propensity to crystallise when stored for prolonged periods.
w/v of a naphthalene formaldehyde condensate surfactant.
We have found that formulations according to the invention surprisingly do not solidify when milled during manufacture and also exhibit a low propensity to crystallise when stored for prolonged periods.
Description
SUSPENSION CONCENTRATE FORMULATION CONTAINING PYRIMETHANIL
This invention relates to liquid formulations of pyrimethanil and methods for their preparation. In particular, the invention relates to suspension concentrate (SC) formulations that contain high proportions of solid pyrimethanil.
Commercial SC formulations comprising the fungicide pyrimethanil include Mythos and Scala . Typically these formulations contain not more than 40% w/v pyrimethanil.
Increasing the amount of pyrimethanil in these formulations above 40% would be advantageous, since it would reduce the cost of transporting a given amount of active ingredient. These savings would be particularly significant where pyrimethanil is transported to remote places where distribution is difficult, such as to tropical zones.
However, increasing the concentration of pyrimethanil in these formulation leads to milling problems during manufacture and crystallisation during storage.
It is therefore an object of the invention to devise an SC formulation system containing concentrations of pyrimethanil significantly greater than 40% without experiencing the abovementioned problems.
According to a first aspect, the invention provides an aqueous SC formulation comprising a) 50 to 80% w/v pyrimethanil, preferably 60 to 80% w/v; b) 0.2 to 5% w/v of a polyoxyethylene-polyoxypropylene block copolymer surfactant, preferably 0.3 to 1.5 %; and c) 0.2 to 5% w/v of a napthalene formaldehyde condensate surfactant, preferably 0.3 to 1.5%.
We have found that formulations according to the invention surprisingly do not solidify when milled during manufacture and also exhibit a low propensity to crystallise when stored for prolonged periods.
Throughout this specification, unless the context requires otherwise, the word "comprise", or variations such as "comprises" or "comprising" will be understood to imply the inclusion of a stated integer or group of integers, but not the exclusion of any other integer or group of integers including method steps.
Preferably component b) has a molecular weight of 6000 to 14 000, especially 9000 to 13000. Further, component b) contains 20 to 80% w/w of polyoxyethylene, especially
This invention relates to liquid formulations of pyrimethanil and methods for their preparation. In particular, the invention relates to suspension concentrate (SC) formulations that contain high proportions of solid pyrimethanil.
Commercial SC formulations comprising the fungicide pyrimethanil include Mythos and Scala . Typically these formulations contain not more than 40% w/v pyrimethanil.
Increasing the amount of pyrimethanil in these formulations above 40% would be advantageous, since it would reduce the cost of transporting a given amount of active ingredient. These savings would be particularly significant where pyrimethanil is transported to remote places where distribution is difficult, such as to tropical zones.
However, increasing the concentration of pyrimethanil in these formulation leads to milling problems during manufacture and crystallisation during storage.
It is therefore an object of the invention to devise an SC formulation system containing concentrations of pyrimethanil significantly greater than 40% without experiencing the abovementioned problems.
According to a first aspect, the invention provides an aqueous SC formulation comprising a) 50 to 80% w/v pyrimethanil, preferably 60 to 80% w/v; b) 0.2 to 5% w/v of a polyoxyethylene-polyoxypropylene block copolymer surfactant, preferably 0.3 to 1.5 %; and c) 0.2 to 5% w/v of a napthalene formaldehyde condensate surfactant, preferably 0.3 to 1.5%.
We have found that formulations according to the invention surprisingly do not solidify when milled during manufacture and also exhibit a low propensity to crystallise when stored for prolonged periods.
Throughout this specification, unless the context requires otherwise, the word "comprise", or variations such as "comprises" or "comprising" will be understood to imply the inclusion of a stated integer or group of integers, but not the exclusion of any other integer or group of integers including method steps.
Preferably component b) has a molecular weight of 6000 to 14 000, especially 9000 to 13000. Further, component b) contains 20 to 80% w/w of polyoxyethylene, especially
2 40 to 80%. In particular, the molecular weight of component b) is nominally 12000 and the amount of polyoxyethylene is nominally 70% w/w.
Preferably component c) is a salt, particularly the sodium salt.
Preferably the formulation also comprises a dispersant, such as a polymethyl methacrylate-polyethylene glycol graft copolymer, preferably having a molecular weight of 20000 to 30000, in amounts of 1 to 10% w/v, preferably 3 to 8%.
A particularly preferred SC formulation comprises a) approximately 60% w/v pyrimethanil, b) approximately 0.5% w/v of an ethyleneoxy-propyleneoxy block co-poiymer surfactant, c) approximately 1 % w/v of sodium naphthalene formaldehyde condensate surfactant, d) approximately 5% w/v polymethyl methacrylate-polyethylene glycol graft copolymer, e) approximately 6% w/v propylene glycol and f) approximately 37.5% w/v water.
Our invention is illustrated, by way of example only, with reference to the following.
Examples A number of formulations of differing composition were prepared. Table 1 shows the components and their concentrations in w/v. In most cases the components are given as their trade name. Their chemical composition and major function are as follows.
AltoxTM 4894 is polyoxyethylene alkyl ether (NPE-free); acts as a dispersant and wetter.
Atlox 4913 is polymethyl methacrylate-polyethylene glycol graft copolymer;
acts as a dispersant.
Atiox 5406B is a blend of anionic and nonionic surfactants; acts as a dispersant and wetter.
MorwetT"' D425 is sodium naphtalene formaldehyde condensate; acts as a dispersant and viscosity modifier.
SynperonicTM PE F127 is a polyoxyethylene-polyoxypropylene block copolymer;
acts as LauropalT"" X1003 is an ethoxylated alcohol; acts as a wetter.
PolyfonTM H is sodium lignosulphonate; acts as a dispersant.
TegoprenT'" 5840 is a copolymer consisting of polymethyl siloxanes and polyoxyethylene-polyoxypropyiene segments; acts as a wetter.
Preferably component c) is a salt, particularly the sodium salt.
Preferably the formulation also comprises a dispersant, such as a polymethyl methacrylate-polyethylene glycol graft copolymer, preferably having a molecular weight of 20000 to 30000, in amounts of 1 to 10% w/v, preferably 3 to 8%.
A particularly preferred SC formulation comprises a) approximately 60% w/v pyrimethanil, b) approximately 0.5% w/v of an ethyleneoxy-propyleneoxy block co-poiymer surfactant, c) approximately 1 % w/v of sodium naphthalene formaldehyde condensate surfactant, d) approximately 5% w/v polymethyl methacrylate-polyethylene glycol graft copolymer, e) approximately 6% w/v propylene glycol and f) approximately 37.5% w/v water.
Our invention is illustrated, by way of example only, with reference to the following.
Examples A number of formulations of differing composition were prepared. Table 1 shows the components and their concentrations in w/v. In most cases the components are given as their trade name. Their chemical composition and major function are as follows.
AltoxTM 4894 is polyoxyethylene alkyl ether (NPE-free); acts as a dispersant and wetter.
Atlox 4913 is polymethyl methacrylate-polyethylene glycol graft copolymer;
acts as a dispersant.
Atiox 5406B is a blend of anionic and nonionic surfactants; acts as a dispersant and wetter.
MorwetT"' D425 is sodium naphtalene formaldehyde condensate; acts as a dispersant and viscosity modifier.
SynperonicTM PE F127 is a polyoxyethylene-polyoxypropylene block copolymer;
acts as LauropalT"" X1003 is an ethoxylated alcohol; acts as a wetter.
PolyfonTM H is sodium lignosulphonate; acts as a dispersant.
TegoprenT'" 5840 is a copolymer consisting of polymethyl siloxanes and polyoxyethylene-polyoxypropyiene segments; acts as a wetter.
3 ReaxT" 85A is sodium lignosulphonate; acts as a dispersant.
SurfynolT" 104-E is tetramethyl decynediol and ethylene glycol; acts mainly as a wetter.
SurfynolT"" 420 is polyoxyethylene (1.3 moles) tetramethyl decynediol; acts as a wetter.
ArylanT"' SBC25 is sodium dodecylbenzene sulphonate; acts as a wetter.
WitconolT"' NS 500 LQ is a nonionic surfactant blend; acts as a dispersant.
SynperonicT"" 91/6 is polyoxyethylene (6 moles) synthetic primary CdCõ
alcohol; acts as a wetter.
EmcolT"' CC9E is polypropylene glycol (9 moles) diethylmonium chloride; acts as a dispersant and viscosity modifier.
Aerosol OT/ STM is dioctyl sodium sulfosuccinate; acts as a wetter.
Each formulation was prepared as follows.
Method All components (except aqueous KelzanTM pregel) are dispersed using a high speed mixer. The dispersion is passed through a bead mili under such conditions to achieve the desired particle size distribution and viscosity. Aqueous Kelzan pregel is added to the milled suspension.
Formulations 1 and 2 are formulations of the invention. The remaining formulations are by way of comparison. Each formulation was analysed in terms of milling performance and extent of crystallisation after 2 weeks storage at 54 C. The results are as follows Milling performance Formulations 3 to 6, 13 to 18, 20 and 24 solidified during milling.
Formulations 1, 2, 7 to 12, 19, 21, 22 and 23 exhibited no milling problems.
SurfynolT" 104-E is tetramethyl decynediol and ethylene glycol; acts mainly as a wetter.
SurfynolT"" 420 is polyoxyethylene (1.3 moles) tetramethyl decynediol; acts as a wetter.
ArylanT"' SBC25 is sodium dodecylbenzene sulphonate; acts as a wetter.
WitconolT"' NS 500 LQ is a nonionic surfactant blend; acts as a dispersant.
SynperonicT"" 91/6 is polyoxyethylene (6 moles) synthetic primary CdCõ
alcohol; acts as a wetter.
EmcolT"' CC9E is polypropylene glycol (9 moles) diethylmonium chloride; acts as a dispersant and viscosity modifier.
Aerosol OT/ STM is dioctyl sodium sulfosuccinate; acts as a wetter.
Each formulation was prepared as follows.
Method All components (except aqueous KelzanTM pregel) are dispersed using a high speed mixer. The dispersion is passed through a bead mili under such conditions to achieve the desired particle size distribution and viscosity. Aqueous Kelzan pregel is added to the milled suspension.
Formulations 1 and 2 are formulations of the invention. The remaining formulations are by way of comparison. Each formulation was analysed in terms of milling performance and extent of crystallisation after 2 weeks storage at 54 C. The results are as follows Milling performance Formulations 3 to 6, 13 to 18, 20 and 24 solidified during milling.
Formulations 1, 2, 7 to 12, 19, 21, 22 and 23 exhibited no milling problems.
4 Extent of crystallisation after storage at 54 C
Formulations 7 to 12, 19, 21, 22 and 23 exhibited crystal growth after 2 weeks at 54 C, this was particularly marked with 11, 19, 21 and 23.
Formulation 2 showed very slight crystallisation.
Formulation 1 showed no crystal growth.
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Formulations 7 to 12, 19, 21, 22 and 23 exhibited crystal growth after 2 weeks at 54 C, this was particularly marked with 11, 19, 21 and 23.
Formulation 2 showed very slight crystallisation.
Formulation 1 showed no crystal growth.
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co M 10 N ~ COO Lf0') . . . . O . . . . . . . . . . M
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Claims (10)
1. An aqueous suspension concentrate formulation comprising:
a) 50 to 80% w/v pyrimethanil, b) 0.2 to 5% w/v of a polyoxyethylene-polyoxypropylene block copolymer surfactant, and c) 0.2 to 5% w/v of a napthalene formaldehyde condensate surfactant.
a) 50 to 80% w/v pyrimethanil, b) 0.2 to 5% w/v of a polyoxyethylene-polyoxypropylene block copolymer surfactant, and c) 0.2 to 5% w/v of a napthalene formaldehyde condensate surfactant.
2. A formulation according to claim 1 wherein component b) has a molecular weight of 6,000 to 14,000.
3. A formulation according to claim 1 wherein component b) has a molecular weight of 9,000 to 13,000.
4. A formulation according to claim 1 wherein component b) contains 20 to 80% w/w of polyoxyethylene.
5. A formulation according to Claim 1 wherein component b) contains 40 to 80% w/w of polyoxyethylene.
6. A formulation according to claim 1 wherein the molecular weight of component b) is 12,000 and the amount of polyoxyethylene is 70% w/w.
7. A formulation according to any one of claims 1 to 6 wherein component c) is a salt.
8. A formulation according to any one of claims 1 to 7 which further comprises a polymethyl methacrylate-polyethylene glycol graft copolymer dispersant.
9. A formulation according to claim 8 wherein the dispersant has a molecular weight of 20,000 to 30,000, in amounts of 1 to 10% w/v.
10. A formulation comprising:
a) approximately 60% w/v pyrimethanil, b) approximately 0.5% w/v of an ethyleneoxy-propyleneoxy block co-polymer surfactant, c) approximately 1 % w/v of sodium naphthalene formaldehyde condensate surfactant, d) approximately 5% w/v polymethyl methacrylatepolyethylene glycol graft copolymer, e) approximately 6% w/v propylene glycol, and f) approximately 37.5% w/v water.
a) approximately 60% w/v pyrimethanil, b) approximately 0.5% w/v of an ethyleneoxy-propyleneoxy block co-polymer surfactant, c) approximately 1 % w/v of sodium naphthalene formaldehyde condensate surfactant, d) approximately 5% w/v polymethyl methacrylatepolyethylene glycol graft copolymer, e) approximately 6% w/v propylene glycol, and f) approximately 37.5% w/v water.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9817354.5A GB9817354D0 (en) | 1998-08-11 | 1998-08-11 | Liquid formulation |
| GB9817354.5 | 1998-08-11 | ||
| PCT/GB1999/002437 WO2000008931A1 (en) | 1998-08-11 | 1999-08-09 | Suspension concentrate formulation containing pyrimethanil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2339622A1 CA2339622A1 (en) | 2000-02-24 |
| CA2339622C true CA2339622C (en) | 2008-02-19 |
Family
ID=10836983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002339622A Expired - Lifetime CA2339622C (en) | 1998-08-11 | 1999-08-09 | Suspension concentrate formulation containing pyrimethanil |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US6559156B1 (en) |
| EP (1) | EP1104238B1 (en) |
| JP (1) | JP4505140B2 (en) |
| KR (1) | KR100641616B1 (en) |
| CN (1) | CN1151720C (en) |
| AP (1) | AP1301A (en) |
| AT (1) | ATE237936T1 (en) |
| AU (1) | AU754127B2 (en) |
| BR (1) | BR9914301B1 (en) |
| CA (1) | CA2339622C (en) |
| CO (1) | CO5210933A1 (en) |
| CZ (1) | CZ292763B6 (en) |
| DE (1) | DE69907211T2 (en) |
| DK (1) | DK1104238T3 (en) |
| ES (1) | ES2192070T3 (en) |
| GB (1) | GB9817354D0 (en) |
| GT (1) | GT199900129A (en) |
| HK (1) | HK1039548B (en) |
| HN (1) | HN1999000135A (en) |
| HU (1) | HU229545B1 (en) |
| ID (1) | ID29098A (en) |
| IL (1) | IL141331A0 (en) |
| IN (1) | IN2001DE00185A (en) |
| MA (1) | MA24956A1 (en) |
| MX (1) | MX217365B (en) |
| NO (1) | NO327734B1 (en) |
| NZ (1) | NZ509802A (en) |
| OA (1) | OA13128A (en) |
| PH (1) | PH11999001989B1 (en) |
| PL (1) | PL196307B1 (en) |
| PT (1) | PT1104238E (en) |
| SI (1) | SI1104238T1 (en) |
| SK (1) | SK284955B6 (en) |
| TR (1) | TR200100422T2 (en) |
| TW (1) | TW575432B (en) |
| WO (1) | WO2000008931A1 (en) |
| ZA (1) | ZA200101056B (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0021786D0 (en) * | 2000-09-05 | 2000-10-18 | Zeneca Ltd | Fungicidal formulations |
| DK2259556T3 (en) * | 2003-05-09 | 2012-09-17 | Freebit As | Audio Headset |
| KR20050047699A (en) * | 2003-11-18 | 2005-05-23 | 주식회사 엘지생명과학 | Fungicidal aqueous suspension concentrate |
| DE102004011006A1 (en) * | 2004-03-06 | 2005-09-22 | Bayer Cropscience Ag | Suspension concentrates based on oil |
| UA93700C2 (en) † | 2006-02-23 | 2011-03-10 | Фмк Корпорейшн | Pesticidal composition, method for producing composition and method for controlling undesirable plants |
| WO2007145221A1 (en) * | 2006-06-13 | 2007-12-21 | Nissan Chemical Industries, Ltd. | Aqueous suspension agricultural chemical composition |
| CN101779638B (en) * | 2009-12-31 | 2012-06-27 | 江苏省绿盾植保农药实验有限公司 | Disinfectant containing pyrimethanil and vinclozolin |
| WO2013026470A1 (en) * | 2011-08-22 | 2013-02-28 | Agriphar S.A. | Aqueous suspension concentrate comprising dodecylguanidine |
| BR102013021474A8 (en) * | 2013-08-22 | 2019-05-21 | Rotam Agrochem Int Co Ltd | new aqueous suspoemulsion and a process for preparing it |
| CN104642354A (en) * | 2013-11-21 | 2015-05-27 | 苏州田园农业技术开发有限公司 | Capsicum seed initiator |
| CN104642352A (en) * | 2013-11-21 | 2015-05-27 | 苏州田园农业技术开发有限公司 | Initiator for rapidly germinating capsicum seeds |
| CN104642353A (en) * | 2013-11-21 | 2015-05-27 | 苏州田园农业技术开发有限公司 | Low temperature resistant capsicum seed initiator |
| CR20170421A (en) * | 2015-03-19 | 2018-04-03 | Valent Biosciences Llc | CONCENTRATED FORMULATIONS OF NATAMICINE IN SUSPENSION |
| CN104855423A (en) * | 2015-05-12 | 2015-08-26 | 柳州市耕青科技有限公司 | Special rot resistant agent for succulent sedum sarmentosum |
| EP3292759A1 (en) * | 2016-09-07 | 2018-03-14 | Bayer CropScience Aktiengesellschaft | Formulations containing fluopyram for the control of nematodes |
| TW202229230A (en) | 2020-10-01 | 2022-08-01 | 美商科迪華農業科技有限責任公司 | Polymorphs of compounds having pesticidal activity |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU193175B (en) * | 1983-07-29 | 1987-08-28 | Budapesti Vegyimuevek | Process for preparing aqueous fungicide suspension containing 2,4'-dichloro-alpha-/pyrimidin-5yl/-diphenyl-methanol as active substance |
| US4875929A (en) | 1986-05-23 | 1989-10-24 | American Cyanamid Company | Aqueous suspension concentrate compositions |
| CA1289065C (en) * | 1986-05-23 | 1991-09-17 | Leonard John Morgan | Aqueous suspension concentrate compositions |
| US4871392A (en) * | 1986-05-23 | 1989-10-03 | American Cyanamid Company | Aqueous suspension concentrate compositions of pendimethalin |
| GB8710105D0 (en) * | 1987-04-29 | 1987-06-03 | Ici Plc | Pesticidal formulations |
| ZA91755B (en) * | 1990-03-05 | 1992-10-28 | Basf Corp | Liquid analogs of certain polyoxyalkylene compounds having a plurality of heteric polyoxypropylene/polyoxyethylene chains as dispersants for pesticidal formulations |
| GB9020207D0 (en) * | 1990-09-15 | 1990-10-24 | Schering Ag | Fungicides |
| JP3086741B2 (en) * | 1991-02-07 | 2000-09-11 | クミアイ化学工業株式会社 | Agricultural and horticultural fungicide composition |
| JP3778527B2 (en) * | 1996-04-09 | 2006-05-24 | アグロカネショウ株式会社 | Stable aqueous suspension composition of 2-amino-3-chloro-1,4-naphthoquinone |
| GB9615158D0 (en) * | 1996-07-19 | 1996-09-04 | Dowelanco | Process for preparing storage-stable pesticide dispersion |
-
1998
- 1998-08-11 GB GBGB9817354.5A patent/GB9817354D0/en not_active Ceased
-
1999
- 1999-08-05 PH PH11999001989A patent/PH11999001989B1/en unknown
- 1999-08-09 SI SI9930235T patent/SI1104238T1/en unknown
- 1999-08-09 DK DK99940284T patent/DK1104238T3/en active
- 1999-08-09 AU AU54283/99A patent/AU754127B2/en not_active Expired
- 1999-08-09 MX MXPA01001525 patent/MX217365B/en unknown
- 1999-08-09 TR TR2001/00422T patent/TR200100422T2/en unknown
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Effective date: 20190809 |